ES2980476T3 - Derivados de tienopiridina y composición farmacéutica que los contiene - Google Patents

Derivados de tienopiridina y composición farmacéutica que los contiene Download PDF

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Publication number: ES2980476T3
Authority: ES; Spain
Prior art keywords: pyridin; methyl; phenyl; oxo; thieno
Prior art date: 2018-03-08
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

ES19770390T

Other languages

English (en)

Spanish (es)

Inventor

Hyunho Lee

Chun-Ho Park

Sun Chul Hur

Jai-Hee Moon

Jae-Sik Shin

Seung-Woo Hong

Yoon-Sun Park

Joseph Kim

Sohee Lee

Hyojin Kim

Hyebin Park

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wellmarker Bio Co Ltd

Original Assignee

Wellmarker Bio Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2018-03-08

Filing date

2019-03-08

Publication date

2024-10-01

2019-03-08 Application filed by Wellmarker Bio Co Ltd filed Critical Wellmarker Bio Co Ltd

2024-10-01 Application granted granted Critical

2024-10-01 Publication of ES2980476T3 publication Critical patent/ES2980476T3/es

Status Active legal-status Critical Current

2039-03-08 Anticipated expiration legal-status Critical

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 29
DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 title description 11
-1 thienopyridine derivative compound Chemical class 0.000 claims abstract description 51
230000000694 effects Effects 0.000 claims abstract description 43
150000003839 salts Chemical class 0.000 claims abstract description 36
102000001253 Protein Kinase Human genes 0.000 claims abstract description 32
108060006633 protein kinase Proteins 0.000 claims abstract description 32
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 31
201000010099 disease Diseases 0.000 claims abstract description 30
238000011282 treatment Methods 0.000 claims abstract description 19
230000002265 prevention Effects 0.000 claims abstract description 14
150000001875 compounds Chemical class 0.000 claims description 220
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
229910052736 halogen Inorganic materials 0.000 claims description 49
150000002367 halogens Chemical class 0.000 claims description 48
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 25
206010028980 Neoplasm Diseases 0.000 claims description 20
201000011510 cancer Diseases 0.000 claims description 18
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
206010009944 Colon cancer Diseases 0.000 claims description 9
229910052705 radium Inorganic materials 0.000 claims description 9
229910052701 rubidium Inorganic materials 0.000 claims description 9
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
239000000654 additive Substances 0.000 claims description 8
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
201000004681 Psoriasis Diseases 0.000 claims description 7
206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
125000002947 alkylene group Chemical group 0.000 claims description 6
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 5
208000001333 Colorectal Neoplasms Diseases 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
206010006187 Breast cancer Diseases 0.000 claims description 4
208000026310 Breast neoplasm Diseases 0.000 claims description 4
230000000996 additive effect Effects 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
206010033128 Ovarian cancer Diseases 0.000 claims description 3
206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
206010060862 Prostate cancer Diseases 0.000 claims description 3
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
206010038389 Renal cancer Diseases 0.000 claims description 3
208000000453 Skin Neoplasms Diseases 0.000 claims description 3
208000005718 Stomach Neoplasms Diseases 0.000 claims description 3
208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
208000002495 Uterine Neoplasms Diseases 0.000 claims description 3
206010017758 gastric cancer Diseases 0.000 claims description 3
201000010536 head and neck cancer Diseases 0.000 claims description 3
208000014829 head and neck neoplasm Diseases 0.000 claims description 3
201000010982 kidney cancer Diseases 0.000 claims description 3
201000007270 liver cancer Diseases 0.000 claims description 3
208000014018 liver neoplasm Diseases 0.000 claims description 3
201000005202 lung cancer Diseases 0.000 claims description 3
208000020816 lung neoplasm Diseases 0.000 claims description 3
208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
201000002528 pancreatic cancer Diseases 0.000 claims description 3
208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
201000000849 skin cancer Diseases 0.000 claims description 3
201000011549 stomach cancer Diseases 0.000 claims description 3
201000002510 thyroid cancer Diseases 0.000 claims description 3
206010046766 uterine cancer Diseases 0.000 claims description 3
ZONFFSSSBCJMPG-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-ethoxy-N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-2-oxopyridine-3-carboxamide Chemical compound CCOC1=C(C(=O)NC2=CC(F)=C(OC3=C4SC(=CC4=NC=C3)C3=NC=C(CNCCOC)C=C3)C=C2)C(=O)N(C=C1)C1=CC=C(Cl)C=C1 ZONFFSSSBCJMPG-UHFFFAOYSA-N 0.000 claims description 2
LVQQAXADCOEAFY-UHFFFAOYSA-N 4-ethoxy-N-[3-fluoro-4-[2-[5-(morpholin-4-ylmethyl)pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound CCOC1=C(C(=O)NC2=CC(F)=C(OC3=C4SC(=CC4=NC=C3)C3=NC=C(CN4CCOCC4)C=C3)C=C2)C(=O)N(C=C1)C1=CC=C(F)C=C1 LVQQAXADCOEAFY-UHFFFAOYSA-N 0.000 claims description 2
QFVBULFWMRQZKW-UHFFFAOYSA-N 4-ethoxy-N-[3-fluoro-4-[2-[5-(morpholin-4-ylmethyl)pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound CCOC1=C(C(=O)NC2=CC(F)=C(OC3=C4SC(=CC4=NC=C3)C3=NC=C(CN4CCOCC4)C=C3)C=C2)C(=O)N(C=C1)C1=CC=CC=C1 QFVBULFWMRQZKW-UHFFFAOYSA-N 0.000 claims description 2
LKFIRSDCHCIKSS-UHFFFAOYSA-N 4-ethoxy-N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(3-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound CCOC1=C(C(=O)NC2=CC(F)=C(OC3=C4SC(=CC4=NC=C3)C3=NC=C(CNCCOC)C=C3)C=C2)C(=O)N(C=C1)C1=CC(F)=CC=C1 LKFIRSDCHCIKSS-UHFFFAOYSA-N 0.000 claims description 2
CWEYLJRAVZNSGW-UHFFFAOYSA-N 4-ethoxy-N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(3-methoxyphenyl)-2-oxopyridine-3-carboxamide Chemical compound CCOC1=C(C(=O)NC2=CC(F)=C(OC3=C4SC(=CC4=NC=C3)C3=NC=C(CNCCOC)C=C3)C=C2)C(=O)N(C=C1)C1=CC(OC)=CC=C1 CWEYLJRAVZNSGW-UHFFFAOYSA-N 0.000 claims description 2
LYKVLRSTJMGUBV-UHFFFAOYSA-N 4-ethoxy-N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound CCOC1=C(C(=O)NC2=CC(F)=C(OC3=C4SC(=CC4=NC=C3)C3=NC=C(CNCCOC)C=C3)C=C2)C(=O)N(C=C1)C1=CC=C(F)C=C1 LYKVLRSTJMGUBV-UHFFFAOYSA-N 0.000 claims description 2
VANZRUICRKHKKD-UHFFFAOYSA-N 4-ethoxy-N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(4-methoxyphenyl)-2-oxopyridine-3-carboxamide Chemical compound CCOC1=C(C(=O)NC2=CC(F)=C(OC3=C4SC(=CC4=NC=C3)C3=NC=C(CNCCOC)C=C3)C=C2)C(=O)N(C=C1)C1=CC=C(OC)C=C1 VANZRUICRKHKKD-UHFFFAOYSA-N 0.000 claims description 2
IFVPBWODUQOFBX-UHFFFAOYSA-N 4-ethoxy-N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-2-oxo-1-[4-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound CCOC1=C(C(=O)NC2=CC(F)=C(OC3=C4SC(=CC4=NC=C3)C3=NC=C(CNCCOC)C=C3)C=C2)C(=O)N(C=C1)C1=CC=C(C=C1)C(F)(F)F IFVPBWODUQOFBX-UHFFFAOYSA-N 0.000 claims description 2
KFCOLWPNPQLLPP-UHFFFAOYSA-N 4-ethoxy-N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound CCOC1=C(C(=O)NC2=CC(F)=C(OC3=C4SC(=CC4=NC=C3)C3=NC=C(CNCCOC)C=C3)C=C2)C(=O)N(C=C1)C1=CC=CC=C1 KFCOLWPNPQLLPP-UHFFFAOYSA-N 0.000 claims description 2
KGRZLPCJGDFXPZ-UHFFFAOYSA-N 4-ethoxy-N-[3-fluoro-4-[2-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C(C)OC1=C(C(N(C=C1)C1=CC=C(C=C1)F)=O)C(=O)NC1=CC(=C(C=C1)OC1=C2C(=NC=C1)C=C(S2)C1=NC=C(C=C1)CN1CCN(CC1)C)F KGRZLPCJGDFXPZ-UHFFFAOYSA-N 0.000 claims description 2
AWRPRJPUFUSQRV-UHFFFAOYSA-N 4-ethoxy-N-[3-fluoro-4-[2-[5-[[2-methoxyethyl(methyl)amino]methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C(C)OC1=C(C(N(C=C1)C1=CC=C(C=C1)F)=O)C(=O)NC1=CC(=C(C=C1)OC1=C2C(=NC=C1)C=C(S2)C1=NC=C(C=C1)CN(C)CCOC)F AWRPRJPUFUSQRV-UHFFFAOYSA-N 0.000 claims description 2
UEAYLSWZZYMPKV-UHFFFAOYSA-N 5-bromo-N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound COCCNCC1=CN=C(C=C1)C1=CC2=NC=CC(OC3=C(F)C=C(NC(=O)C4=CC(Br)=CN(C4=O)C4=CC=C(F)C=C4)C=C3)=C2S1 UEAYLSWZZYMPKV-UHFFFAOYSA-N 0.000 claims description 2
UAQLSJWPLQGMFW-UHFFFAOYSA-N 5-chloro-N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound COCCNCC1=CN=C(C=C1)C1=CC2=NC=CC(OC3=C(F)C=C(NC(=O)C4=CC(Cl)=CN(C4=O)C4=CC=C(F)C=C4)C=C3)=C2S1 UAQLSJWPLQGMFW-UHFFFAOYSA-N 0.000 claims description 2
SBDCJKPFBKECEN-UHFFFAOYSA-N N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound COCCNCC1=CN=C(C=C1)C1=CC2=NC=CC(OC3=C(F)C=C(NC(=O)C4=CC=CN(C4=O)C4=CC=C(F)C=C4)C=C3)=C2S1 SBDCJKPFBKECEN-UHFFFAOYSA-N 0.000 claims description 2
PXZCVBQTKJNRIY-UHFFFAOYSA-N N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(4-fluorophenyl)-4-methoxy-2-oxopyridine-3-carboxamide Chemical compound FC=1C=C(C=CC=1OC1=C2C(=NC=C1)C=C(S2)C1=NC=C(C=C1)CNCCOC)NC(=O)C=1C(N(C=CC=1OC)C1=CC=C(C=C1)F)=O PXZCVBQTKJNRIY-UHFFFAOYSA-N 0.000 claims description 2
CURGTYVNEHTWDV-UHFFFAOYSA-N N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(4-fluorophenyl)-4-methyl-2-oxopyridine-3-carboxamide Chemical compound FC=1C=C(C=CC=1OC1=C2C(=NC=C1)C=C(S2)C1=NC=C(C=C1)CNCCOC)NC(=O)C=1C(N(C=CC=1C)C1=CC=C(C=C1)F)=O CURGTYVNEHTWDV-UHFFFAOYSA-N 0.000 claims description 2
NXUODRWFXMNITR-UHFFFAOYSA-N N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(4-fluorophenyl)-5-methyl-2-oxopyridine-3-carboxamide Chemical compound COCCNCC1=CN=C(C=C1)C1=CC2=NC=CC(OC3=C(F)C=C(NC(=O)C4=CC(C)=CN(C4=O)C4=CC=C(F)C=C4)C=C3)=C2S1 NXUODRWFXMNITR-UHFFFAOYSA-N 0.000 claims description 2
COXXJQGTUOBHSS-UHFFFAOYSA-N N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(4-fluorophenyl)-6-methyl-2-oxopyridine-3-carboxamide Chemical compound FC=1C=C(C=CC=1OC1=C2C(=NC=C1)C=C(S2)C1=NC=C(C=C1)CNCCOC)NC(=O)C=1C(N(C(=CC=1)C)C1=CC=C(C=C1)F)=O COXXJQGTUOBHSS-UHFFFAOYSA-N 0.000 claims description 2
GDQSZMFRMNXJBK-UHFFFAOYSA-N N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-2-(4-fluorophenyl)-3-oxopyridazine-4-carboxamide Chemical compound FC=1C=C(C=CC=1OC1=C2C(=NC=C1)C=C(S2)C1=NC=C(C=C1)CNCCOC)NC(=O)C=1C(N(N=CC=1)C1=CC=C(C=C1)F)=O GDQSZMFRMNXJBK-UHFFFAOYSA-N 0.000 claims description 2
SJHHJUYEBYTNNE-UHFFFAOYSA-N N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-2-(4-fluorophenyl)-5-methyl-3-oxopyridazine-4-carboxamide Chemical compound FC=1C=C(C=CC=1OC1=C2C(=NC=C1)C=C(S2)C1=NC=C(C=C1)CNCCOC)NC(=O)C=1C(N(N=CC=1C)C1=CC=C(C=C1)F)=O SJHHJUYEBYTNNE-UHFFFAOYSA-N 0.000 claims description 2
WACIAMHZBIQEAD-UHFFFAOYSA-N N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound FC=1C=C(C=CC=1OC1=C2C(=NC=C1)C=C(S2)C1=NC=C(C=C1)CNCCOC)NC(=O)C=1C(N(C=CC=1)C1=CC=CC=C1)=O WACIAMHZBIQEAD-UHFFFAOYSA-N 0.000 claims description 2
WBRANJSAHCFZMB-UHFFFAOYSA-N N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-3-oxo-2-phenylpyridazine-4-carboxamide Chemical compound FC=1C=C(C=CC=1OC1=C2C(=NC=C1)C=C(S2)C1=NC=C(C=C1)CNCCOC)NC(=O)C=1C(N(N=CC=1)C1=CC=CC=C1)=O WBRANJSAHCFZMB-UHFFFAOYSA-N 0.000 claims description 2
VRSPQJVMCVQUHO-UHFFFAOYSA-N N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-4-methoxy-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound COCCNCC1=CN=C(C=C1)C1=CC2=NC=CC(OC3=C(F)C=C(NC(=O)C4=C(OC)C=CN(C4=O)C4=CC=CC=C4)C=C3)=C2S1 VRSPQJVMCVQUHO-UHFFFAOYSA-N 0.000 claims description 2
WAPQXVUOOSLPFI-UHFFFAOYSA-N N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-4-methyl-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound COCCNCC1=CN=C(C=C1)C1=CC2=NC=CC(OC3=C(F)C=C(NC(=O)C4=C(C)C=CN(C4=O)C4=CC=CC=C4)C=C3)=C2S1 WAPQXVUOOSLPFI-UHFFFAOYSA-N 0.000 claims description 2
XNRNKJNBPKODHH-UHFFFAOYSA-N N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-5-methyl-3-oxo-2-phenylpyridazine-4-carboxamide Chemical compound FC=1C=C(C=CC=1OC1=C2C(=NC=C1)C=C(S2)C1=NC=C(C=C1)CNCCOC)NC(=O)C=1C(N(N=CC=1C)C1=CC=CC=C1)=O XNRNKJNBPKODHH-UHFFFAOYSA-N 0.000 claims description 2
VQRCBMAZYVKSKI-UHFFFAOYSA-N N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-6-methyl-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound COCCNCC1=CN=C(C=C1)C1=CC2=NC=CC(OC3=C(F)C=C(NC(=O)C4=CC=C(C)N(C4=O)C4=CC=CC=C4)C=C3)=C2S1 VQRCBMAZYVKSKI-UHFFFAOYSA-N 0.000 claims description 2
108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 2
102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 2
SHTFHGKFUJAPEF-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-ethoxy-N-[3-fluoro-4-[2-[5-(morpholin-4-ylmethyl)pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-2-oxopyridine-3-carboxamide Chemical compound CCOC1=C(C(=O)NC2=CC(F)=C(OC3=C4SC(=CC4=NC=C3)C3=NC=C(CN4CCOCC4)C=C3)C=C2)C(=O)N(C=C1)C1=CC=C(Cl)C=C1 SHTFHGKFUJAPEF-UHFFFAOYSA-N 0.000 claims 1
AVQMZXNIWUWSRB-UHFFFAOYSA-N 1-(4-chlorophenyl)-N-[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-4-methoxy-2-oxopyridine-3-carboxamide Chemical compound COCCNCC1=CN=C(C=C1)C1=CC2=NC=CC(OC3=C(F)C=C(NC(=O)C4=C(OC)C=CN(C4=O)C4=CC=C(Cl)C=C4)C=C3)=C2S1 AVQMZXNIWUWSRB-UHFFFAOYSA-N 0.000 claims 1
TVJIXVOEXRTCBG-UHFFFAOYSA-N N-[2-chloro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(4-fluorophenyl)-4-methoxy-2-oxopyridine-3-carboxamide Chemical compound COCCNCC1=CN=C(C=C1)C1=CC2=NC=CC(OC3=CC(Cl)=C(NC(=O)C4=C(OC)C=CN(C4=O)C4=CC=C(F)C=C4)C=C3)=C2S1 TVJIXVOEXRTCBG-UHFFFAOYSA-N 0.000 claims 1
MRPKBMAVEHCXRU-UHFFFAOYSA-N N-[3-chloro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(4-fluorophenyl)-4-methoxy-2-oxopyridine-3-carboxamide Chemical compound COCCNCC1=CN=C(C=C1)C1=CC2=NC=CC(OC3=C(Cl)C=C(NC(=O)C4=C(OC)C=CN(C4=O)C4=CC=C(F)C=C4)C=C3)=C2S1 MRPKBMAVEHCXRU-UHFFFAOYSA-N 0.000 claims 1
WYTGPUFDTMRMGN-UHFFFAOYSA-N tert-butyl N-[[6-[7-[4-[[4-ethoxy-1-(4-fluorophenyl)-2-oxopyridine-3-carbonyl]amino]-2-fluorophenoxy]thieno[3,2-b]pyridin-2-yl]pyridin-3-yl]methyl]-N-(2-methoxyethyl)carbamate Chemical compound C(C)OC1=C(C(N(C=C1)C1=CC=C(C=C1)F)=O)C(=O)NC1=CC(=C(OC2=C3C(=NC=C2)C=C(S3)C2=CC=C(C=N2)CN(C(OC(C)(C)C)=O)CCOC)C=C1)F WYTGPUFDTMRMGN-UHFFFAOYSA-N 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 abstract description 13
238000003786 synthesis reaction Methods 0.000 description 88
230000015572 biosynthetic process Effects 0.000 description 87
238000002360 preparation method Methods 0.000 description 81
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WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
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COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
102000020233 phosphotransferase Human genes 0.000 description 1
230000002165 photosensitisation Effects 0.000 description 1
239000003504 photosensitizing agent Chemical class 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
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235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
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239000011591 potassium Substances 0.000 description 1
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238000001953 recrystallisation Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000009256 replacement therapy Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
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230000035945 sensitivity Effects 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
230000011664 signaling Effects 0.000 description 1
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229910052708 sodium Inorganic materials 0.000 description 1
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235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
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239000000600 sorbitol Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
210000000130 stem cell Anatomy 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
229960001052 streptozocin Drugs 0.000 description 1
ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000011477 surgical intervention Methods 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
239000003277 telomerase inhibitor Substances 0.000 description 1
NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
229960001278 teniposide Drugs 0.000 description 1
OOBULOSOIWVGDP-UHFFFAOYSA-N tert-butyl N-[[6-[7-[4-[(4-ethoxy-2-oxo-1-phenylpyridine-3-carbonyl)amino]-2-fluorophenoxy]thieno[3,2-b]pyridin-2-yl]pyridin-3-yl]methyl]-N-(2-methoxyethyl)carbamate Chemical compound N(CCOC)(CC1=CN=C(C=C1)C=1SC2=C(C=1)N=CC=C2OC1=C(F)C=C(NC(=O)C=2C(=O)N(C=CC=2OCC)C2=CC=CC=C2)C=C1)C(=O)OC(C)(C)C OOBULOSOIWVGDP-UHFFFAOYSA-N 0.000 description 1
XSWLVMSPIAFKRJ-UHFFFAOYSA-N tert-butyl n-[(6-bromopyridin-3-yl)methyl]-n-(2-methoxyethyl)carbamate Chemical compound COCCN(C(=O)OC(C)(C)C)CC1=CC=C(Br)N=C1 XSWLVMSPIAFKRJ-UHFFFAOYSA-N 0.000 description 1
RYRXEENRCNVKPA-UHFFFAOYSA-N tert-butyl n-[[6-(7-chlorothieno[3,2-b]pyridin-2-yl)pyridin-3-yl]methyl]-n-(2-methoxyethyl)carbamate Chemical compound N1=CC(CN(CCOC)C(=O)OC(C)(C)C)=CC=C1C1=CC2=NC=CC(Cl)=C2S1 RYRXEENRCNVKPA-UHFFFAOYSA-N 0.000 description 1
MUBHRMREUBOKBA-UHFFFAOYSA-N tert-butyl n-[[6-[7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl]pyridin-3-yl]methyl]-n-(2-methoxyethyl)carbamate Chemical compound N1=CC(CN(CCOC)C(=O)OC(C)(C)C)=CC=C1C1=CC2=NC=CC(OC=3C(=CC(=CC=3)[N+]([O-])=O)F)=C2S1 MUBHRMREUBOKBA-UHFFFAOYSA-N 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
229960001196 thiotepa Drugs 0.000 description 1
238000002877 time resolved fluorescence resonance energy transfer Methods 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
229960000303 topotecan Drugs 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
230000005747 tumor angiogenesis Effects 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
230000005751 tumor progression Effects 0.000 description 1
208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
231100000588 tumorigenic Toxicity 0.000 description 1
230000000381 tumorigenic effect Effects 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
239000008371 vanilla flavor Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
230000029663 wound healing Effects 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4365—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

ES19770390T 2018-03-08 2019-03-08 Derivados de tienopiridina y composición farmacéutica que los contiene Active ES2980476T3 (es)

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KR20180027300		2018-03-08
PCT/KR2019/002743 WO2019182274A1 (fr)	2018-03-08	2019-03-08	Dérivés de thiénopyridine et composition pharmaceutique le comprenant

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US (1)	US11447500B2 (fr)
EP (1)	EP3762392B1 (fr)
JP (1)	JP6955630B2 (fr)
KR (1)	KR102221689B1 (fr)
CN (1)	CN111295386B (fr)
AU (1)	AU2019237715B2 (fr)
CA (1)	CA3072169C (fr)
ES (1)	ES2980476T3 (fr)
WO (1)	WO2019182274A1 (fr)

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US20220235064A1 (en) *	2019-08-02	2022-07-28	Wellmarker Bio Co., Ltd.	Oxo-pyridine fusion ring derivative and pharmaceutical composition comprising same
JP2023513675A (ja) *	2020-02-06	2023-04-03	ウェルマーカー・バイオ・カンパニー・リミテッド	Ｋｒａｓ変異に関連する癌の予防または治療のための医薬組成物
KR20210111711A (ko) *	2020-03-03	2021-09-13	웰마커바이오 주식회사	Kras 돌연변이 및 활성화된 ron이 존재하는 암의 예방 또는 치료용 약학 조성물
JP2023526443A (ja) *	2020-05-18	2023-06-21	ウェルマーカーバイオカンパニーリミテッド	Ｒｏｎ変異が関与する非小細胞肺がんの予防又は治療用医薬組成物及びその使用方法
US20230202992A1 (en) *	2020-05-18	2023-06-29	Wellmarker Bio Co., Ltd.	Pharmaceutical composition for preventing or treating small-cell lung cancer associated with ron mutants and method using same
KR20210142555A (ko) *	2020-05-18	2021-11-25	웰마커바이오 주식회사	Ron 돌연변이와 관련된 췌장암 예방 또는 치료용 약학 조성물 및 이를 이용한 방법
CA3212769A1 (fr) *	2021-03-26	2022-09-29	Laura Carzaniga	Derives de tetrahydrothieno pyridine utilises en tant qu'inhibiteurs de ddr
TWI812301B (zh) *	2021-06-24	2023-08-11	南韓商Ｌｇ化學股份有限公司	作為ｒｏｎ抑制劑之新穎尿素衍生物化合物
KR102495191B1 (ko)	2022-10-13	2023-02-06	주식회사 웃샘	전열교환기를 이용한 주거용 실내환경 복합제어장치

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JO2787B1 (en)	2005-04-27	2014-03-15	امجين إنك,	Alternative amide derivatives and methods of use
JP2009526761A (ja) *	2006-01-30	2009-07-23	アレイバイオファーマ、インコーポレイテッド	ヘテロ二環式チオフェン化合物および使用の方法
SI2089364T1 (sl)	2006-11-08	2013-10-30	Bristol-Myers Squibb Company	Spojine piridinona
PL2183254T3 (pl) *	2007-08-29	2017-10-31	Methylgene Inc	Inhibitory aktywności białkowej kinazy tyrozynowej
ES2593279T3 (es) *	2007-08-29	2016-12-07	Methylgene Inc.	Procesos e intermedios para preparar inhibidores de cinasa heterocíclicos condensados
TWI365185B (en)	2008-07-24	2012-06-01	Lilly Co Eli	Amidophenoxyindazoles useful as inhibitors of c-met
US20130090327A1 (en) *	2011-09-30	2013-04-11	Methylgene Inc.	Inhibitors of Protein Tyrosine Kinase Activity
KR101350006B1 (ko) *	2012-09-06	2014-02-13	씨제이제일제당 (주)	피리돈 유도체를 포함하는 단백질 키나제 억제제
US11946934B2 (en) *	2014-09-03	2024-04-02	Wellmarker Bio Co., Ltd.	Biomarker for predicting the sensitivity to a protein kinase inhibitor and a use thereof
EP3120851A1 (fr) *	2015-07-21	2017-01-25	Pangaea Biotech S.L.	4-amino-6- (2,6-dichlorophényl) -8-methyl-2-(phénylamino) -pyrido[2,3-d]pyrimidin-7-(8h)-one pour le traitement de cancers solides

2019
- 2019-03-08 WO PCT/KR2019/002743 patent/WO2019182274A1/fr not_active Ceased
- 2019-03-08 AU AU2019237715A patent/AU2019237715B2/en active Active
- 2019-03-08 US US16/638,668 patent/US11447500B2/en active Active
- 2019-03-08 JP JP2020523268A patent/JP6955630B2/ja active Active
- 2019-03-08 ES ES19770390T patent/ES2980476T3/es active Active
- 2019-03-08 EP EP19770390.3A patent/EP3762392B1/fr active Active
- 2019-03-08 CN CN201980005460.4A patent/CN111295386B/zh active Active
- 2019-03-08 KR KR1020190026798A patent/KR102221689B1/ko active Active
- 2019-03-08 CA CA3072169A patent/CA3072169C/fr active Active

Also Published As

Publication number	Publication date
KR20190106802A (ko)	2019-09-18
KR102221689B1 (ko)	2021-03-02
EP3762392A4 (fr)	2021-09-15
CA3072169A1 (fr)	2019-09-26
CN111295386B (zh)	2022-09-06
JP6955630B2 (ja)	2021-10-27
AU2019237715B2 (en)	2021-01-28
EP3762392A1 (fr)	2021-01-13
BR112020008663A2 (pt)	2020-10-06
EP3762392B1 (fr)	2024-05-15
JP2021500378A (ja)	2021-01-07
US11447500B2 (en)	2022-09-20
CA3072169C (fr)	2022-04-19
CN111295386A (zh)	2020-06-16
AU2019237715A1 (en)	2020-04-16
WO2019182274A1 (fr)	2019-09-26
US20210317133A1 (en)	2021-10-14

Publication	Publication Date	Title
ES2980476T3 (es)	2024-10-01	Derivados de tienopiridina y composición farmacéutica que los contiene
JP2024138293A (ja)	2024-10-08	バイオマーカー型治療用組成物
JP6139527B2 (ja)	2017-05-31	二環式複素芳香族化合物
JP5426544B2 (ja)	2014-02-26	ピリミジニル−ピリダジノン誘導体
WO2013097280A1 (fr)	2013-07-04	Composés de quinoline et de cinnoline et application associée
CN102548987B (zh)	2014-04-16	作为激酶抑制剂的氟取代化合物及其使用方法
EA022064B1 (ru)	2015-10-30	Гетариламинонафтиридины в качестве ингибиторов атф-связывающих белков
US20220235064A1 (en)	2022-07-28	Oxo-pyridine fusion ring derivative and pharmaceutical composition comprising same
CN115028648B (zh)	2024-08-30	三并环化合物及其药物组合物和应用
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